Work

Biosynthesis of Polycyclic Natural Products from Conjugated Polyenes via Tandem Isomerization and Pericyclic Reactions

Year: 2023

Type: article

Abstract: We report biosynthetic pathways that can synthesize and transform conjugated octaenes and nonaenes to complex natural products. The biosynthesis of (-)-PF1018 involves an enzyme PfB that can control the regio-, stereo-, and periselectivity of multiple reactions starting from a conjugated octaene. Using PfB as a lead, we discovered a homologous enzyme, BruB, that facilitates diene isomerization, tandem 8π-6π-electrocyclization, and a 1,2-divinylcyclobutane Cope rearrangement to generate a new-to-nature compound.

Source: Journal of the American Chemical Society

DOI: 10.1021/jacs.3c02380

Authors: Kanji Niwa, Masao Ohashi, Kaili Xie, Chen-Yu Chiang, Cooper S. Jamieson, Michio Sato, Kenji Watanabe, Fang Liu, K. N. Houk, Yi Tang

Institutions: University of California, Los Angeles, Nanjing Agricultural University, Shizuoka University, University of Shizuoka

Language: English

Topic: Microbial Natural Products and Biosynthesis

Subfield: Pharmacology

Field: Medicine

Domain: Health Sciences

Open Access status: green

Funders: Uehara Memorial Foundation, Japan Society for the Promotion of Science, National Institute of General Medical Sciences, National Center for Research Resources

Awards: G1756637430, Identification of target molecules based on self-resistance gene-directed genome mining, Understanding a mechanism of an onset of colorectal cancer by colibactin and finding compounds inhibiting colibactin biosynthetic enzymes, G4305609567, G863947390

OpenAlex ID: W4380422075

FWCI: 2.334

Cites: 41

Cited by: 18

Related to: 10